283 



The other constituents of the leaf oil of C. Macleayana were dextro-rotatory 

 pinene, highh' dextro-rotatory limonene with some dipentene, a small amount of 

 ester, and a sesquiterpene which indicated cadinene strongly, although it was not 

 lfevo-rotator\'. 



The specific gravit}' of the crude oil at|f°C. =o-8484; rotation «,, -|- 42-5°; 

 and refractive index at 20° C. = 1-4791. The saponification number, after boiling, 

 was g-g, equal to 3-5 per cent, of esters. In the cold, with three hours' contact, 

 the saponification number was 9-2, equal to 3-2 per cent, of esters, thus indicating 

 that geranyl-acetate was the principal ester, and although the identity of the alcohol 

 was not determined with certainty, yet it had the geraniol odour strongly marked. 



On redistilling 100 c.c. of the oil, but little was obtained boiling below 160° C. 

 Between 160° and 170°, 50 per cent, distilled ; between 170° and 180°, 26 per cent. ; 

 between 180° and 240°, 8 per cent. ; between 240° and 270°, 11 per cent. 



The specific gravity of the first fraction at 22° C. = 0-8372 ; of the second, 

 0-8379; of the third, 0-862; of the fourth, o-gi67. The rotation of the first 

 fraction, a-Q= + 46-2°; of the second, -|- 56-0°; of the third, -|- 57-3°; of the 

 fourth, 4- 16-6°. 



The first fraction was again distilled, when ig c.c. was obtained boiling 

 below 160° C, and 18 c.c. between 160° and 168° C. The specific gravity at 22° C. 

 of the first fraction was 0-8413; of the second, 0-837. The rotation of the first 

 fraction, ^0= -1- 42-3°; of the second, -|- 52-6°. 



The Pinene. — The portion which came over below 160° was again distilled, 

 and 7 c.c. collected, boiling between 155° and 157° C. This was largelv pinene. 

 It had a specific gravity at 22° C. = 0-8443; rotation, aB= -|- 37-4°; and refractive 

 index, = 1-4733. A small amount of the nitrosochloride was obtained \\ith it, 

 which, when finally purified, melted at 107-108° C. 



The Menthene Fraction. — The oil boiling between 160-168° was added to 

 the remainder in the flask, and the distillation continued, when the oil which 

 came over below 162° C. was separated; 10 c.c. was thus obtained, boiling between 

 162° and 165°. This had specific gravity at 22° C. = 0-837; rotation, «!,= -|- 58-7°; 

 and refractive index at 22° C. = 1-4703. It probabty contained some limonene, 

 but had a ^-ery marked odour of menthene ; and this, together with the low specific 

 gravity and the low refractive index, indicated the presence of a member of this 

 group. Although the results do not correspond closely to those of the known 

 menthenes, yet, even among the comparatively pure members considerable differ- 

 ences occur, as, for instance, between menthene and car^'0-menthene. It was 

 not possible, with the amount of material at our disposal, to carry the separation 

 and purification further, and the complete identity of this hydrocarbon thus 

 remains in abevance. 



